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You’ve reached mid-life. Doubts arise about your commitment to the business. Five key questions will help you clarify your career goals.

According to ancient Greek myth, when young Theseus had proved he was ready, he set out on a long, perilous journey from his mother’s house to the city of Athens, where his father, Aegeus, was king. If he survived the journey he would be found a worthy successor to his father’s throne. Like all travelers before him, Theseus had to overcome many trials along the way, assuring that only the hardiest would reach the goal.

Perhaps the most difficult encounter was the ordeal of the Procrustean bed. Nearing Athens, travelers would be set upon by a terrible giant, Procrustes, who would drag them into his lair and strap them to his iron bed. If they were too short, Procrustes would stretch them to fit the exact proportions of the bed. If they were too long, parts would be lopped off. Those who survived were freed to complete their journey, albeit altered by the ordeal. But Theseus tricked Procrustes into lying on his own bed, where he killed him by his own methods. On reaching Athens he received a hero’s welcome and the crown of his birthright.

All myths that stand the test of time express some universal truth about human nature. Theseus’s ordeal symbolizes the dangers and opportunities facing anyone who embarks on a quest to fulfill their dreams. The Athens sought by many modern-day travelers is corporate success. On this journey, no one can escape the Procrustean bed of corporate expectations and demands. Parts of themselves will be unnaturally stretched, and valued parts may be cut off, in order to achieve power and success. Although painful, this process has its rewards, and for many the benefits outweigh the costs. Up to a point. Up until mid-life.

Mid-life is a time of reevaluation, when everyone, whether consciously or not, begins to take stock of themselves and their journey. This reevaluation typically lasts for a few years, sometimes longer, and can include work, family, friends, community, religion, and personal pursuits. Many people end up reaffirming choices made earlier, while others may head in a new direction.

Men and women who entered the family business in their 20s or 30s begin to step back and take a close look at what has become of their personal dreams. They are drawn to revisit their decision to join the family enterprise, to reappraise the unique advantages and stresses they have faced as leaders or members of the business, and to contemplate their future. They are coming face to face with the Procrustean bed of their own corporate culture, seeing more clearly the parts of themselves that have been painfully stretched, or cut off or abandoned. They can now weigh the costs and benefits of these choices. The remainder of their lives, and the lives of those around them, can be powerfully shaped by how well they deal with this mid-life transition.

But how does a mid-career man or woman in a family firm assess his or her situation? Five critical questions, addressed in light of the Procrustean bed, can help focus the inquiry. The case of two sibling co-owners (composite characters drawn from actual family businesses) also helps show how these questions can clarify mid-career uncertainty.

Carla Johnson was 10 years old, her brother Paul was 8, when a younger brother, Sam, was born with Down syndrome. Although the whole family knew it would have to adjust to the special needs of a handicapped child, no one could have predicted how much this event would change all of their lives.

Sam gradually became the center of the family’s attention. As his parents focused on his special medical and educational needs, Carla and Paul helped out as much as they could. Although brother and sister sometimes resented the extra responsibilities, they also loved Sam and slowly both began to reveal their unique strengths and talents in helping to care for him. Carla, more serious and focused, liked to coach Sam on his schoolwork and do special projects with him. Paul, more fun loving, liked to play with Sam and invent stories and games that could help Sam’s learning. All in all, the “Sammy Project,” as they came to call it, brought a close family even closer.

Then, when Carla was in the second year of an MBA program and Paul was a senior in college, their father was suddenly killed in a car accident, a tragic turning point for the whole family. Carla and Paul both finished their studies and found jobs close to home so they could help their mother care for Sam. Gradually, however, as their mother aged and their careers became more demanding, everyone realized that Sam would need more help than they could provide at home. Reluctantly, they began looking for a group home.

Discouraged by what they saw, Carla and Paul finally voiced what was on both their minds: “We could create a better group home for Sam than these guys!” This was the seed that grew to become Johnson Enterprises.

Carla and Paul initially proved to be ideally suited for their new enterprise. Through their father’s business dealings, they already had an extensive network of business contacts.

With Carla’s business acumen, they were able to get the financial backing to start their first group home. Paul had a knack for developing educational and social programs for residents and was always a source of levity when lightness was needed. Over the next 15 years, the company grew to a network of homes within their state, with a potential to expand into other markets. At ages 42 and 40, Carla and Paul were proud of what they had accomplished—a successful business and a good home for Sam.

And yet, like many other executives at this juncture of their lives, just when they could expect to begin enjoying the fruits of their labor, Carla and Paul found a tension growing between them. Carla had developed a tough and demanding leadership style, earning the respect of the management team, if not their affection. Paul was good at team building and developing staff skills, but tended to defer to Carla for major decisions. Carla began to think her brother was too soft, while Paul often felt his sister was too tough and was alienating their best staff. Both were sure they were “right.” The management team and their families knew something was definitely “wrong.” Sam summed it up well one day at a family gathering when he said, “What’s wrong with my best buddies? Why do you fight all the time?”

Although slow to recognize the difficulties at work, both were more aware of struggles in their personal lives. Carla had married in her mid-30s, but had decided not to have children. She and her husband worked long hours at Johnson Enterprises and found little time for much else. Paul and his wife had three children, and now found himself weary with the toll his growing business responsibilities was taking on his family.

Carla and Paul recognized that the continued success of the business was in jeopardy and, secretly, worried about their personal lives. Indeed, they were facing some of the deep- seated concerns that often erupt at mid-life, and finally decided to seek help. They participated in an executive coaching program that helped them identify these mid-life issues and guided them through the needed reevaluation. In this work, Carla and Paul were directed to ponder the following five critical questions.

1. What parts of you have fit the Procrustean bed well?

I begin the mid-career assessment by taking stock of a person’s talents, abilities, and interests that fit naturally with their chosen work within the family business. Most executives are acutely aware of their perceived weaknesses and shortcomings, but my experience has been that they are hesitant about revealing their true personal strengths and talents to others, or even to themselves, as if they might begin to relax or slack off. However, identifying strengths, skills, and abilities is useful for constructing a cognitive life raft, so that later the individual can more safely enter the turbulent waters of what has not fit well.

To gather more accurate, honest data, we use both objective and subjective means. On the subjective side, I ask questions such as: What accomplishments have you particularly enjoyed at work? What aspects of your work are you especially good at? What do you most look forward to when you wake up in the morning? What do you enjoy doing when you are not at work? Are you surprised to find yourself embracing aspects of the work you vowed never to do?

On the objective side, individuals need to be shown a clear picture of what they have actually accomplished and learned. This might include a chronological review of a person’s career, examination of job performance measures, and information from others who work closely with them. Various 360-degree assessments, such as the Center for Creative Leadership’s Benchmarks Survey or the Campbell Leadership Index, elicit feedback about a person’s performance from an executive’s superiors, peers, and direct reports (hence the term 360 degree). In many cases I interview these people and keyfamily members to gain a fuller picture. The data are organized into descriptive and objective summary tables and discussed in depth with the manager.

As a first step, these measures tell individuals what has been a good fit between initial career choices and the proven strengths and abilities that have brought them to this point in their career. In all likelihood, these assets will be the foundation for future accomplishments and career choices.

Carla and Paul had shaped a business and careers that seemed to fit them pretty well. Carla’s business savvy had guided the early development of Johnson Enterprises and was essential to its continuing growth. She was astute about the company’s financial workings and was good with long-term strategy. Paul complemented his sister well, skillfully managing people and providing a creative spark when the business needed it. He had a distinct ability to understand people and motivate them to work well as a group.

They agreed to participate in a mid-career review that included several psychological instruments and a 360-degree assessment questionnaire. Although a bit reluctant to fill out the surveys at first, when staff members understood that the feedback would remain anonymous they welcomed the opportunity to evaluate their top leaders. They hoped that this process would help Carla and Paul function better as a leadership team.

The feedback on Carla’s and Paul’s strengths confirmed many of their own perceptions, but there were a few surprises. The management team had indicated that Paul often seemed to have a strong personal vision of the company’s future and that they wanted him to be more forthcoming and public with it. Carla was surprised to see that, although practically everyone saw her as a tough-minded leader, some were able to see her inner sensitivity, her genuine concern for employees and especially for the residents. Carla was secretly pleased that a number of respondents noted that she always seemed to take the time to greet and talk with the residents whenever she could.

When Carla and Paul agreed to share the general results of their feedback with each other, Paul was reminded of Carla’s caring side, as well as the deep affection they shared for their brother, Sam. Paul’s results showed Carla that even though his cognitive style was quite different from hers, he had more vision and stronger analytic gifts than she had thought. Carla and Paul began to feel less polarized. Each of them was a more complex combination of talents.

2. What parts of you may have been unnaturally stretched to fit the Procrustean bed?

Most career choices require individuals to develop and use part of themselves that may not feel natural or even preferable. After 15 to 20 years of work experience, people at mid-career have learned much about what they are good at, as well as what areas of their work life always seem to be a painful stretch. Executives can begin to choose whether they want to continue trying to develop these skills and abilities, or whether it is time to relax, accept certain personal limitations, and develop compensatory strategies.

To examine this, we look at the more difficult aspects of a person’s work. I might ask open, subjective questions such as: What parts of your work seem to deaden your spirit? What do you most avoid? What aspects of your company and your work disappoint you, and what aspects of yourself are you most discouraged about? The data collected during the 360 process also can give an objective view of what others identify as consistent problem areas. Once these questions are examined we can then ask: Are these issues something you should work on, or, given your unique personality, is it even realistic to expect improvement in some of these areas? To help reach an answer, I sometimes turn to personality questionnaires (such as the Myers-Briggs Type Indicator) and vocational inventories (such as the Campbell Interests and Skills Survey). These instruments can give a clearer picture of innate personality and vocational preferences that indicate areas less amenable to change, as well as areas one could stretch further.

It is hard for anyone to look honestly at this kind of information, but denying limitations can be a recipe for future trouble. Stories abound of promising executives who got sidetracked into dead-end positions, or seeming superstars who quickly fizzled in the harsh realities of a changing business climate. In most cases, these individuals could not look honestly at shortcomings and make the needed adjustments. Along with middle age can come the wisdom that it is often more rewarding to go down a path that does not stretch you far beyond your capabilities.

Carla and Paul had had both stretched themselves in the rapid development of their company. They had each exceeded their own initial expectations and were pleased with what they had accomplished together. But often our greatest strengths can become liabilities if overused, and Carla and Paul were in danger of ignoring certain problem areas. Carla got some tough feedback from her management team about her abrasive leadership style, as well as her tendency to be abrupt and occasionally explode under pressure. Paul’s respondents let him know he needed to take a visibly stronger position in the leadership of the company and that he often was not viewed as an equal member of the senior team.

Carla and Paul began to accept the truth in the feedback, which was initially difficult to hear. Furthermore, when they shared the feedback with each other they were able to see more objectively, through the eyes of others, their own strengths and weaknesses. They began to understand how the emerging conflict between them was hurting the whole management team and that accepting each other’s limitations could reduce the tension between them.

3. What valued parts of yourself have been cut off or abandoned to fit the Procrustean bed?

At mid-life we start to become aware of parts of our personality that may have been sacrificed in order to negotiate the journey toward career success. In the rosy glow of early career decisions and successes, young executives often believe they have all the time in the world to postpone personal dreams or cherished goals. An almost universal blind spot of youth is the uncompromising limits of time. There always seems to be a tomorrow. One of the major triggers from the mid-life transition is the growing recognition that time is a limited commodity.

People are often bewildered by the intensity of the issues that seem to arise during the mid-life transition. All the more so for successful executives because these emotions seem to hit when the erratic gyrations of earlier career development have given way to a relative calm and steadiness. As in all phases of human development, it is precisely at these times that hidden or neglected aspects of oneself begin to cry out for attention. If these “cut-off” parts continue to be ignored, they begin to emerge on their own as seemingly irrational thoughts, impulsive actions, or stormy emotional outbursts. As painful as it may be to revisit lost dreams, if they are brought to light for conscious reexamination there may be ways of integrating aspects of them back into one’s life.

Mining forgotten aspects of one’s hopes and dreams can often be a rich source of inspiration and renewal for the later stages of the journey.

This was the most difficult question for Carla to address. For the first time, she fully allowed herself to wonder about something always on the edges of her awareness: Why did she sacrifice so much for other people? First it was her parents and her brother Sam. Now she felt she was carrying responsibilities for Paul, with little time left for herself.

Her marriage seemed stagnant, and she even began to wonder about her decision not to have children.

In recent years Carla had become much more driven and was aware that her drive was beginning to have a harsher edge. Was this related to her habit of putting the needs of others and the business before her own? I encouraged her to keep this question open within herself and when she felt comfortable, to begin to share aspects of this exploration with her husband and Paul. Although it was difficult for her at first, Carla did begin to share this, and was surprised to see that both men treated this new vulnerability with kindness and respect. Both seemed relieved to see this side of her and were supportive of her struggle. She slowly began to see that her more sensitive and warm parts, while needing to be pushed aside when growing the business, could now be a source of strength in all arenas of her life. Indeed, Carla was reminded that it was her love of her brother Sam that was the founding vision of Johnson Enterprises.

4. Have you arrived at your true Athens?

When starting a career, most people set off down a general path toward a vague and distant goal. Each individual, however, has formulated their own unique dream of Athens somewhere inside. These internal visions of success are shaped by a complex interaction of internal and external pressures, much of which is out of conscious awareness. Deeply entwined with one’s natural and inherent personal preferences are a myriad of other influences: the expectations of parents and siblings, the voice of a powerful teacher or mentor, or simply the random turn of life’s events.

It takes great effort to stay in touch with our dreams during the early phases of career development. All too often on our journey toward Athens we can get lost in a sea of external pressures, altered by the Procrustean bed of the business climate, societal norms, or the collective dream of the family business. The loss of one’s own dream is the loss of a personal compass, and this confusion of direction will often be experienced at mid-life as a bewildering onset of career inertia or waning motivation. Theologian and philosopher Thomas Moore has said, “Symptoms are the voices of the soul.” In this fourth question, I use the painful reactions that arise from the earlier questions to explore the deeper meaning of these reactions. What are these “symptoms” trying to tell us about lost directions and lost dreams?

Here, the executive and I work together to reconnect him or her with the earlier visions of success. Although these may seem somewhat grandiose or idealistic when viewed from a mid-life perspective, often an ongoing theme can be found, a thread that weaves its way from childhood to early adulthood and through to middle age, which expresses a more true and deep desire. Quite possibly it is this thread that one will want to use to begin to weave the future tapestry of one’s later career.

This question turned out to be the most difficult for Paul, and yet yielded the most fruit. Trusting his older sister’s drive and determination, Paul had joined forces with her without a great deal of reflection. He had majored in psychology and education in college, but had no clear sense of direction in either field when he and Carla started Johnson Enterprises. Choosing to follow the lead of an older or more competent sibling in a family enterprise is not uncommon, and often a practical choice, but Paul’s case was more one made by default.

This indecision had now come back to haunt him. In our work, he began to question whether he had been following his own wishes or simply reacting to those of his sister, mother, and long-deceased father. His query deepened to older issues: What would he have done if Sam hadn’t been born with Down syndrome, if his father hadn’t died when he did, if he had gone on to graduate school? He and Carla had certainly accomplished what they had set out to do; they had provided a fine home for Sam, were providing income to help their mother, were supporting their families well, and were leading a successful business enterprise. But were these his goals?

Many people instinctively want to turn away from tough questions that raise old, hard issues, or perhaps give them a passing glance and rush to premature closure. But Paul stuck with it, and in a way that neither of us could have predicted, he discovered his old love of psychology. He renewed his reading and exploration in this area, and over time, began to realize that his devotion to his mother, brother, sister, wife, and children was a fundamental personal value of his that was directly linked to an older, half-formed dream to serve others through education or psychology. Paul ultimately decided that continuing to build the family enterprise was a meaningful way for him to serve both his family and others in the community and to honor his earlier dream.

5. Do you want to live in Athens, or does the quest continue?

Up to this point, the review process tends to be more of a reactive exploration of choices previously made. The final question requires a proactive approach to future options. This exploration is generally the most subjective, since there are no tests that can tell someone what direction to take in life. We engage in an ongoing Socratic dialogue. And I listen closely to what is being said as we talk about the individual’s future in order to identify underlying assumptions, premises, and preconceptions that need to be examined more closely. It is my experience, almost universally, that a person already has answers to personal questions formulated somewhere deep inside. My task is to help guide their emergence into awareness. At the end of the review, some individuals discover they need to make difficult life changes, pursuing goals that might not meet the family’s expectations, or disrupting the plans of others. Other people will reaffirm their commitment to familiar pathways. Either way, if executives have reflected honestly on these questions and stayed open to considering options, there is a much better chance of moving forward on the journey with renewed meaning and purpose.

Having done the hard work of the previous questions, Carla and Paul were ready to ask themselves about the future. Both were concluding their executive coaching sessions with a greater awareness of the strengths and weaknesses in their leadership style and a fresh vision for Johnson Enterprises. They decided to work on improving the performance of the senior leadership group, by first strengthening their own working relationship, then developing and empowering the whole leadership team. They had renewed their shared goal of creating better residential facilities for people with special needs. Alongside this re-commitment to the business, Carla was finding more personal time for herself, creating a space for Paul to step forward. Paul was coming into his own, finding ways to integrate his creative and fun-loving nature with his growing authority.

Again it was Sam who had the last word. As Carla and Paul were rushing off from a lunch visit one day to attend a meeting, Sam turned to a fellow resident and said, “See those two good buddies? That’s my brother and sister!” What I have found, time and again, in working with executives at mid-career is that the aspects of their self that were sacrificed to fit the Procrustean bed of early career success are precisely the parts that need to be revived in order to negotiate the latter phases of their journey. Carla believed that she needed to distance herself at work from her human warmth while aggressively growing the business, and yet came to discover that this hidden sensitive side was exactly what was needed to empower the leadership team in the years ahead. Paul, whose more naturally cooperative style often led him to defer to Carla’s more commanding presence, was discovering that this style of leadership carried its own strength and command. Increasingly, he was able to assert himself in his own way and was learning how to lead in a cooperative parity with his sister.

These five questions do not lessen the stresses of mid-career reevaluation, and may actually heighten anxiety for a time by drawing attention to underlying conflicts and half- forgotten dreams. Indeed, the questions are designed to use the intensity of these issues to help conduct a personal inventory of one’s career within the family business, and ultimately to emerge with greater clarity of vision and purpose.

Katherine Grady, Ph.D. is a Partner at Lansberg • Gersick in New Haven, Connecticut. Formerly on the faculty at Yale University and the Center for Creative Leadership, she has been a family business consultant for over 20 years. Her work focuses on continuity planning, governance design, and leadership development.

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